Stannous chloride dihydrate → HCID 86675703, compound

HRID 68661Notes

Reaction equation

HRID 68661 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([N+:11]([O-])=O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.O.O.Cl[Sn]Cl>C(O)(=O)C.Cl>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 866757042-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 86675703HCID 86675703, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 2-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine (21.76 g, 89.54 mmol) in acetic acid (108.8 mL) and concentrated hydrogen chloride (108.8 mL) was added dichlorotin dihydrate (101.0 g, 447.7 mmol). The reaction mixture was left to stir for 1 hour at ambient temperature. Reaction mixture was quenched by addition of 2M NaOH solution and the aqueous extracted with EtOAc (×3). Organic layer was dried (MgSO4), filtered and concentrated in vacuo. The resulting solid was washed with saturated NaHCO3 solution and the solid collected, washed with water and dried to give 2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-amine (10.4 g, 54.6%). 1H NMR (400.0 MHz, DMSO) δ 11.50 (br s, 1H), 8.22 (s, 1H), 7.16 (s, 1H) and 4.35 (br s, 2H) ppm; MS (ES+) 214.79

Workup

  1. waitThe reaction mixture was left
  2. customReaction mixture
  3. customwas quenched by addition of 2M NaOH solution
  4. extractionthe aqueous extracted with EtOAc (×3)
  5. dry with materialOrganic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washThe resulting solid was washed with saturated NaHCO3 solution
  9. customthe solid collected
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-1af6c1e2df6b41f98fcb22f4cb51defc
Source dataset
uspto-grants-2014_09
Patent number
US08822469B2

Reaction notes

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